Friedelin

Base Information

• Chemical Name: Friedelin
• CAS No.: 559-74-0
• Molecular Formula: C30H50O
• Molecular Weight: 426.726
• European Community (EC) Number: 209-205-1
• UNII: AK21264UAD
• DSSTox Substance ID: DTXSID101015732
• Nikkaji Number: J17.557I
• Wikipedia: Friedelin
• Wikidata: Q15410972
• Metabolomics Workbench ID: 53182
• ChEMBL ID: CHEMBL485998
• Mol file: 559-74-0.mol

Synonyms:24,25,26-trinoroleanan-3-one, 5,9,13-trimethyl-, (4beta,5beta,8alpha,9beta,10alpha,13alpha,14beta)-;friedelan-3-one;friedelanone;friedelin;friedeline

Chemical Property of Friedelin

Chemical Property:

• Vapor Pressure: 2.86E-09mmHg at 25°C
• Melting Point: 262-265 °C(lit.)
• Refractive Index: 1.502
• Boiling Point: 477.2 °C at 760 mmHg
• Flash Point: 233.9 °C
• PSA: 17.07000
• Density: 0.963 g/cm³
• LogP: 8.45700
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 9.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 426.386166214
• Heavy Atom Count: 31
• Complexity: 781

Purity/Quality:

98%,99%, ^*data from raw suppliers

Friedelin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)C)C)C)C)C
• Isomeric SMILES: C[C@H]1C(=O)CC[C@@H]2[C@@]1(CC[C@H]3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C)C)C)C)C
• Uses: Friedelin is a flavonoid extract which displays radical scavenging and anti-typhoid activity. Friedelin can be used as a starting material in the synthesis of:Friedel-3-enol acetate, friedel-2-oxo-3-enol acetate, friedel-2-ene derivatives and friedelin ketoxime.Oxygenated friedelin derivatives as potent DNA topoisomerase IIα inhibitors.Its 1,4-pyrazine derivatives as potent antimicrobial agents.

Technology Process of Friedelin

There total 40 articles about Friedelin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

friedelin oxime (6938-92-7) → friedelin (559-74-0)

Guidance literature:

With hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 6h;

Reference yield: 73.0%

D:A-friedo-olean-21-ene-3-one → friedelin (559-74-0)

Guidance literature:

With hydrogen; platinum(IV) oxide; In acetic acid; for 15h;

DOI:10.1016/0031-9422(82)83043-4

Reference yield: 60.0%

3,3-ethylenedioxyfriedelin → friedelin (559-74-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 12h; Heating;

upstream raw materials:

epifriedelanol

friedelan-3-oxo-2α-acetate

4-epi-friedelin

2α-bromofriedel-3-one

Downstream raw materials:

friedelinol

epifriedelanol

D:A-friedo-oleanane

4-oxa-3,4-secofriedelan-3-oic acid

Refernces

• 1、 Chang, Churng-Werng,Wu, Tien-Shung,Hsieh, Yih-Shou,Kuo, Sheng-Chu,Lee Chao, Pei-Dawn. "Terpenoids of Syzygium formosanum". . p. 327 - 328. Retrieved 1999.
• 2、 Ghosh, Pranab,Chakraborty, Prasanta. "Denomination of 2-bromo-3-keto triterpenoids using N,N-dimethylaniline". experimental part. p. 1037 - 1039. Retrieved 2012/04/04.
• 3、 Ganguly, Nemai C.,Nayek, Subhasish,Barik, Sujoy Kumar,Dutta, Sanjoy. "Aqueous hydrogen peroxide activated by ammonium heptamolybdate catalyst - A mild clean effective reagent system for the deprotection of oximes, semicarbazones and phenylhydrazones at room temperature". body text. p. 711 - 716. Retrieved 2009/12/05.